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Updated: Jun 21, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction
Ruben L H Andringa1, Nittert Marinus1, Daan V Bunt1
1Stratingh Institute for Chemistry, University of Groningen Nijenborgh 7, 9747 AG Groningen The Netherlands M.D.Witte@rug.nl A.J.Minnaard@rug.nl.
Abstract:
Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell Mycobacterium tuberculosis and does not inhibit growth of the bacterium.
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